Use AI to reverse-engineer the best card strategy for any trip

Reading Time: 4 min

It’s taken me a long time to get on board with AI, but I’ve finally found a use case that can make earning and redeeming points and miles a bit more efficient. If you use an AI tool like Claude or ChatGPT, you can reverse-engineer the best credit card for a specific trip.

Start by entering your trip information and current list of travel credit cards, then request a detailed report on how to optimize your credit card strategy. You can then easily identify which credit card to open before you start booking your travel without having to compare a dozen different cards yourself.

I’m heading to Amsterdam in late 2026, so I got a full analysis on how to strategically use credit cards for this vacation.

Here’s a sample prompt you can input into your AI tool of choice:

I'm planning a trip and want you to help me find the best credit card strategy for it. Here are my trip details:

Destination: [City, Country]
Travel dates: [Month and approximate dates]
Departure city: [Your city]
Trip length: [# of nights]

Estimated spend breakdown:
Flights: $[amount]
Hotel: $[amount] for [# nights] at [hotel brand if known]
Dining: $[amount]
Activities & tours: $[amount]
Transport (local): $[amount]
Shopping/misc: $[amount]

Preferred airlines (if any): [airline names]
Hotel loyalty programs (if any): [program names]
Credit cards I currently hold: [list all your cards]

Based on this, please:

1. Identify the single best new credit card to open before this trip, factoring in the welcome bonus and how I'd spend on this trip to meet the minimum spend.
2. Estimate total points/miles I'd earn from the welcome bonus + trip spend, and show the math.
3. Recommend the best way to redeem those points for this trip (flight, hotel, or combo), including the transfer partner and the estimated value per point.
4. For my existing cards, tell me which one to use for each spending category on this trip to maximize points.
5. Flag any risks: blackout dates, transfer timelines, minimum spend difficulty, or redemption pitfalls I should know before I book.

Supercharge your points with the new Bilt credit card lineup

FROM OUR PARTNERS AT BILT Bilt just leveled up in a huge way. With the launch of Bilt 2.0, you can now ​earn up to an incredible 1.25x points on rent and mortgages​. Even better, they’ve introduced creative new features like the "Points Accelerator" which lets you ​turn Bilt Cash into an amazing 2x or 3x points multiplier on everyday purchases​. From welcome bonuses to elite status benefits, these three new cards are designed to reward you heavily for the spending you’re already doing. We’ve mapped out all the exciting new benefits and built a fun, easy decision tree to help you claim your ultimate upgrade.

Explore the new Bilt lineup

Before I entered this prompt into Claude, I asked it to estimate my expenses for a week-long trip to Amsterdam from Charlotte, North Carolina, at the end of the year. Claude beats out the competition when it comes to visuals — here’s the chart it provided for my trip.

I think this is a reasonable estimate of spending, so I used these values along with the prompt above. Claude recommended that I apply for the Chase Ink Business Preferred card. I like this recommendation — I’ve actually considered applying for it for some time now.

Then, it gave me a breakdown of which card to use on which purchases:

Finally, it anticipated how much I’d earn on my trip purchases:

In case you missed it...

​Points Path members' top 10 Prime Day picks

AI can give you recommendations and an outline, but you’re always responsible for double-checking the information it gives you. For instance, Claude told me to use my Chase Sapphire Reserve to pay for transit purchases because these “code” as travel and would earn 3x Ultimate Rewards points. But Chase removed the Sapphire Reserve’s 3x general travel bonus category in 2025, so these purchases would now earn just 1 point per dollar.

Similarly, Claude recommended I use the Ink Business Preferred on a hotel to earn 3x Ultimate Rewards points. While this would make sense if I were working toward the welcome bonus, I’d earn 5x Membership Rewards points using my American Express Platinum Card to book prepaid stays through Amex Travel or 6x bonus Marriott Bonvoy points with my Marriott Bonvoy Bevy if I chose a Marriott property, so those would be a better bet.

It also recommended I transfer all of my points to Flying Blue, even if an economy award costs far less than my total point balance. I’m not sure why it recommended this, since it’s risky to keep your rewards in an airline account that can be subject to no-notice devaluations. You should only transfer exactly what you need to book your flight.

All of this to say, I like Claude’s recommendation. The Ink Business Preferred would allow me to earn 3x on general travel purchases, which is better than anything else in my wallet. From my test, I enjoyed the baseline recommendation and structure of the analysis.

If you want to replicate this for yourself, I recommend exporting the report as an Excel file and swapping out the information as needed to build a more complete (and accurate) plan for your trip.

This compact device provides trusted security wherever you stay

This inexpensive lock ensures your safety in the comfort of your hotel room, and can even buy time in case of an emergency. The door alarm can also help alert you to potential danger.

Get it at Amazon